1-Hydroxybenzotriazole → (6S)-6-(5-chloro-2-methoxybenzyl)-1-(2,4,6-trimethoxybenzyl)-1,4-diazepan-2,5-dione

HRID 554828Notes

Reaction equation

HRID 554828 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH3:33])=[C:6]([CH:31]=1)[CH2:7][C@@H:8]([CH2:16][NH:17][CH2:18][C:19]1[C:24]([O:25][CH3:26])=[CH:23][C:22]([O:27][CH3:28])=[CH:21][C:20]=1[O:29][CH3:30])[C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH3:33])=[C:6]([CH:31]=1)[CH2:7][C@H:8]1[CH2:16][N:17]([CH2:18][C:19]2[C:24]([O:25][CH3:26])=[CH:23][C:22]([O:27][CH3:28])=[CH:21][C:20]=2[O:29][CH3:30])[C:13](=[O:15])[CH2:12][NH:11][C:9]1=[O:10]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67460156HCID 67460156, compound

Product 1

HCID 66935303(6S)-6-(5-chloro-2-methoxybenzyl)-1-(2,4,6-trimethoxybenzyl)-1,4-diazepan-2,5-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of N-{(2S)-2-(5-chloro-2-methoxybenzyl)-3-[(2,4,6-trimethoxybenzyl)amino]propanoyl}glycine (1g) in acetonitrile (30 ml), 1-hydroxy benzotriazole (421 mg) was added at room temperature. The mixture was stirred at 40° C. for 20 minutes, then N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (598 mg) was added to the reaction solution, and the mixture was stirred for 2 hours. After the reaction solution was concentrated in vacuo, toluene was added to the obtained residue, and the resulting mixture was washed with 6% aqueous sodium bicarbonate and saturated brine. The organic layer was concentrated in vacuo, then the obtained residue was purified by silica gel column chromatography to obtain the title compound (894 mg) as a colorless crystal.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. concentrationAfter the reaction solution was concentrated in vacuo, toluene
  3. additionwas added to the obtained residue
  4. washthe resulting mixture was washed with 6% aqueous sodium bicarbonate and saturated brine
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c73109fc85b946e7971aeebbc131558b
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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